CA2599843C - Selective glycosidase inhibitors, methods of making inhibitors, and uses thereof - Google Patents

Selective glycosidase inhibitors, methods of making inhibitors, and uses thereof Download PDF

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Publication number
CA2599843C
CA2599843C CA2599843A CA2599843A CA2599843C CA 2599843 C CA2599843 C CA 2599843C CA 2599843 A CA2599843 A CA 2599843A CA 2599843 A CA2599843 A CA 2599843A CA 2599843 C CA2599843 C CA 2599843C
Authority
CA
Canada
Prior art keywords
thiazoline
dideoxy
glucopyranoso
pyrano
thiazole
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Fee Related
Application number
CA2599843A
Other languages
English (en)
French (fr)
Other versions
CA2599843A1 (en
Inventor
Matthew Macauley
David Vocadlo
Garrett Whitworth
Keith Stubbs
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Simon Fraser University
Original Assignee
Simon Fraser University
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Simon Fraser University filed Critical Simon Fraser University
Priority to CA2819464A priority Critical patent/CA2819464A1/en
Publication of CA2599843A1 publication Critical patent/CA2599843A1/en
Application granted granted Critical
Publication of CA2599843C publication Critical patent/CA2599843C/en
Anticipated expiration legal-status Critical
Expired - Fee Related legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00

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  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • General Chemical & Material Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Diabetes (AREA)
  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • Genetics & Genomics (AREA)
  • Biotechnology (AREA)
  • Hospice & Palliative Care (AREA)
  • Obesity (AREA)
  • Hematology (AREA)
  • Endocrinology (AREA)
  • Emergency Medicine (AREA)
  • Psychiatry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Saccharide Compounds (AREA)
  • Pyrane Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
CA2599843A 2005-03-01 2006-03-01 Selective glycosidase inhibitors, methods of making inhibitors, and uses thereof Expired - Fee Related CA2599843C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CA2819464A CA2819464A1 (en) 2005-03-01 2006-03-01 Selective glycosidase inhibitors, methods of making inhibitors, and uses thereof

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US65687805P 2005-03-01 2005-03-01
US60/656,878 2005-03-01
PCT/CA2006/000300 WO2006092049A1 (en) 2005-03-01 2006-03-01 Selective glycosidase inhibitors, methods of making inhibitors, and uses thereof

Related Child Applications (1)

Application Number Title Priority Date Filing Date
CA2819464A Division CA2819464A1 (en) 2005-03-01 2006-03-01 Selective glycosidase inhibitors, methods of making inhibitors, and uses thereof

Publications (2)

Publication Number Publication Date
CA2599843A1 CA2599843A1 (en) 2006-09-08
CA2599843C true CA2599843C (en) 2013-08-27

Family

ID=36940808

Family Applications (2)

Application Number Title Priority Date Filing Date
CA2599843A Expired - Fee Related CA2599843C (en) 2005-03-01 2006-03-01 Selective glycosidase inhibitors, methods of making inhibitors, and uses thereof
CA2819464A Abandoned CA2819464A1 (en) 2005-03-01 2006-03-01 Selective glycosidase inhibitors, methods of making inhibitors, and uses thereof

Family Applications After (1)

Application Number Title Priority Date Filing Date
CA2819464A Abandoned CA2819464A1 (en) 2005-03-01 2006-03-01 Selective glycosidase inhibitors, methods of making inhibitors, and uses thereof

Country Status (7)

Country Link
US (1) US20080287375A1 (https=)
EP (2) EP1869060B1 (https=)
JP (1) JP5154954B2 (https=)
CN (1) CN101208352B (https=)
AU (1) AU2006220187B2 (https=)
CA (2) CA2599843C (https=)
WO (1) WO2006092049A1 (https=)

Families Citing this family (48)

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WO2006016904A2 (en) * 2004-04-14 2006-02-16 Uab Research Foundation Activators of hexosamine biosynthesis as inhibitors of injury induced by ischemia or hemorrhagic shock
CN107253970A (zh) * 2006-08-31 2017-10-17 西蒙·弗雷瑟大学 选择性糖苷酶抑制剂及其用途
AU2007291870B2 (en) 2006-08-31 2012-12-06 Simon Fraser University Selective glycosidase inhibitors and uses thereof
GB0622702D0 (en) * 2006-11-15 2006-12-27 Univ Dundee Selective glycosidase inhibitors
US8518903B2 (en) 2007-04-19 2013-08-27 University of Pittsburgh—of the Commonwealth System of Higher Education Use of toll-like receptor-9 agonists
EP2321289A4 (en) * 2008-08-01 2011-11-16 Univ Fraser Simon SELECTIVE GLYCOSIDASE HEMMER AND ITS USE
CA2732335A1 (en) 2008-08-01 2010-02-04 Simon Fraser University Selective glycosidase inhibitors and uses thereof
CA2737267A1 (en) * 2008-09-16 2010-04-08 Simon Fraser University Selective glycosidase inhibitors and uses thereof
WO2011140640A1 (en) * 2010-05-11 2011-11-17 Simon Fraser University Selective glycosidase inhibitors and uses thereof
US10668092B2 (en) 2010-09-24 2020-06-02 The John Hopkins University Compositions and methods for treatment of inflammatory disorders
US9072760B2 (en) 2010-09-24 2015-07-07 University of Pittsburgh—of the Commonwealth System of Higher Education TLR4 inhibitors for the treatment of human infectious and inflammatory disorders
WO2012040719A2 (en) * 2010-09-24 2012-03-29 University Of Pittsburgh - Of The Commonwealth System Of Higher Education Novel tlr4 inhibitors for the treatment of human infectious and inflammatory disorders
US8933040B2 (en) 2010-11-08 2015-01-13 Craig A. Coburn Selective glycosidase inhibitors and uses thereof
US8901087B2 (en) * 2010-11-08 2014-12-02 Merck Sharp & Dohme Corp. Selective glycosidase inhibitors and uses thereof
TW201249848A (en) 2010-11-08 2012-12-16 Merck Sharp & Dohme Selective glycosidase inhibitors and uses thereof
WO2012061972A1 (en) * 2010-11-08 2012-05-18 Alectos Therapeutics Inc. Selective glycosidase inhibitors and uses thereof
WO2012088425A2 (en) 2010-12-22 2012-06-28 University Of Pittsburgh - Of The Commonwealth System Of Higher Education Gap junction-enhancing agents for treatment of necrotizing enterocolitis and inflammatory bowel disease
RU2609210C2 (ru) * 2010-12-23 2017-01-31 Алектос Терапьютикс Инк. Селективные ингибиторы гликозидазы и их применение
EP2688899B1 (en) 2011-03-24 2017-02-22 Alectos Therapeutics Inc. Selective glycosidase inhibitors and uses thereof
EP2691407B1 (en) 2011-03-31 2017-02-22 Alectos Therapeutics Inc. Selective glycosidase inhibitors and uses thereof
WO2012129802A1 (en) * 2011-03-31 2012-10-04 Alectos Therapeutics Inc. Pyrano[3,2-d]thiazol derivatives and uses as selective glycosidase inhibitors thereof
US9701693B2 (en) 2011-06-27 2017-07-11 Alectos Therapeutics Inc. Selective glycosidase inhibitors and uses thereof
EP2726468B1 (en) * 2011-06-27 2017-04-12 Alectos Therapeutics Inc. Selective glycosidase inhibitors and uses thereof
BR112013033098B8 (pt) 2011-06-27 2021-03-23 Alectos Therapeutics Inc inibidores de glicosidade seletivos e usos dos mesmos
US9126957B2 (en) 2011-08-18 2015-09-08 Merck Sharp & Dohme Corp. Selective glycosidase inhibitors and uses thereof
ES2568603T3 (es) * 2011-08-25 2016-05-03 Merck Patent Gmbh Pirano[3,2-d][1,3]tiazol como inhibidores de glicosidasas
EP2847199B1 (en) 2012-05-08 2017-10-25 Merck Sharp & Dohme Corp. Permeable glycosidase inhibitors and uses thereof
EP2890675A4 (en) 2012-08-31 2016-01-13 Alectos Therapeutics Inc GLYCOSIDASE INHIBITORS AND USES THEREOF
EP2890676B1 (en) 2012-08-31 2018-12-05 Alectos Therapeutics Inc. Glycosidase inhibitors and uses thereof
WO2014052453A1 (en) 2012-09-25 2014-04-03 University Of Pittsburgh - Of The Commonwealth System Of Higher Education Oral therapy of necrotizing enterocolitis
KR20150079711A (ko) * 2012-10-31 2015-07-08 알렉토스 테라퓨틱스 인크. 글리코시다아제 저해제 및 이의 용도
WO2014100934A1 (en) * 2012-12-24 2014-07-03 Merck Sharp & Dohme Corp. Glycosidase inhibitors and uses thereof
WO2014171206A1 (ja) * 2013-04-17 2014-10-23 Yuasa Tomoyuki 糖尿病治療薬の新規なスクリーニング方法
KR102043337B1 (ko) 2014-08-28 2019-11-11 아셰뉴론 에스아 글리코시다제 저해제
US11261183B2 (en) 2016-02-25 2022-03-01 Asceneuron Sa Sulfoximine glycosidase inhibitors
CA3014572C (en) 2016-02-25 2023-10-03 Asceneuron S.A. Acid addition salts of piperazine derivatives
KR20180132629A (ko) 2016-02-25 2018-12-12 아셰뉴론 에스아 글리코시다제 저해제
AU2017222964B2 (en) 2016-02-25 2020-01-02 Asceneuron S. A. Glycosidase inhibitors
US11213525B2 (en) 2017-08-24 2022-01-04 Asceneuron Sa Linear glycosidase inhibitors
WO2020039027A1 (en) 2018-08-22 2020-02-27 Asceneuron S. A. Pyrrolidine glycosidase inhibitors
JP7407171B2 (ja) 2018-08-22 2023-12-28 エースニューロン・ソシエテ・アノニム グリコシダーゼ阻害剤として有用なピペラジン誘導体のコハク酸付加塩及びフマル酸付加塩
WO2020039029A1 (en) 2018-08-22 2020-02-27 Asceneuron S. A. Spiro compounds as glycosidase inhibitors
WO2020039028A1 (en) 2018-08-22 2020-02-27 Asceneuron S. A. Tetrahydro-benzoazepine glycosidase inhibitors
CN114524854B (zh) * 2022-02-25 2023-05-26 中国农业大学 一种糖基芳香环碳苷衍生物及其制备方法与应用
WO2024083820A1 (en) 2022-10-18 2024-04-25 Institut National de la Santé et de la Recherche Médicale Method and composition for determining the level of o-glcnacylation in horses
CN116376875B (zh) * 2023-03-03 2024-02-23 云南师范大学 耐热性提高的n-乙酰氨基葡萄糖苷酶突变体及其应用
CN116555229B (zh) * 2023-05-25 2024-09-20 云南师范大学 N-乙酰氨基葡萄糖苷酶突变体、重组表达载体及菌和应用
CN118086249B (zh) * 2024-01-24 2024-12-06 云南师范大学 一种协同提高酶活和热稳定性的n-乙酰氨基葡萄糖苷酶突变体及其制备与应用

Family Cites Families (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB9818732D0 (en) * 1998-08-27 1998-10-21 Univ Portsmouth Collection of compounds
US6774140B1 (en) * 1999-05-11 2004-08-10 The Scripps Research Institute Iminocyclitol inhibitors of hexoaminidase and glycosidase
US7105320B2 (en) * 2001-03-14 2006-09-12 Denki Kagaku Kogyo Kabushiki Kaisha Process for producing hyaluronic acid or its derivative
US20070066543A1 (en) * 2003-05-22 2007-03-22 The Hospital For Sick Children Treatment of tay sachs or sandhoff diseases by enhancing hexosaminidase activity
AU2007291870B2 (en) * 2006-08-31 2012-12-06 Simon Fraser University Selective glycosidase inhibitors and uses thereof
CA2732335A1 (en) * 2008-08-01 2010-02-04 Simon Fraser University Selective glycosidase inhibitors and uses thereof
EP2321289A4 (en) * 2008-08-01 2011-11-16 Univ Fraser Simon SELECTIVE GLYCOSIDASE HEMMER AND ITS USE
CA2737267A1 (en) * 2008-09-16 2010-04-08 Simon Fraser University Selective glycosidase inhibitors and uses thereof
WO2011140640A1 (en) * 2010-05-11 2011-11-17 Simon Fraser University Selective glycosidase inhibitors and uses thereof
US8933040B2 (en) * 2010-11-08 2015-01-13 Craig A. Coburn Selective glycosidase inhibitors and uses thereof
RU2609210C2 (ru) * 2010-12-23 2017-01-31 Алектос Терапьютикс Инк. Селективные ингибиторы гликозидазы и их применение
EP2688899B1 (en) * 2011-03-24 2017-02-22 Alectos Therapeutics Inc. Selective glycosidase inhibitors and uses thereof
EP2691407B1 (en) * 2011-03-31 2017-02-22 Alectos Therapeutics Inc. Selective glycosidase inhibitors and uses thereof

Also Published As

Publication number Publication date
EP2436687A1 (en) 2012-04-04
CA2819464A1 (en) 2006-09-08
EP1869060A4 (en) 2009-08-12
US20080287375A1 (en) 2008-11-20
WO2006092049A1 (en) 2006-09-08
AU2006220187A1 (en) 2006-09-08
JP5154954B2 (ja) 2013-02-27
CN101208352B (zh) 2013-08-07
CA2599843A1 (en) 2006-09-08
EP1869060A1 (en) 2007-12-26
AU2006220187B2 (en) 2012-11-08
CN101208352A (zh) 2008-06-25
JP2008531604A (ja) 2008-08-14
EP1869060B1 (en) 2012-08-15

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Effective date: 20180301